BOC-D-SER-OME

Base Information

• Chemical Name: BOC-D-SER-OME
• CAS No.: 95715-85-8
• Molecular Formula: C9H17NO5
• Molecular Weight: 219.238
• Hs Code.: 29241990
• Mol file: 95715-85-8.mol

Synonyms:(R)-Methyl2-(tert-butoxycarbonylamino)-3-hydroxypropanoate;tert-Butyl[(R)-1-(methoxycarbonyl)-2-hydroxyethyl]carbamate;

Chemical Property of BOC-D-SER-OME

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid
• Vapor Pressure: 1.94E-06mmHg at 25°C
• Refractive Index: n20/D 1.453(lit.)
• Boiling Point: 354.3 °C at 760 mmHg
• PKA: 10.70±0.46(Predicted)
• Flash Point: 168.1 °C
• PSA: 84.86000
• Density: 1.149 g/cm³
• LogP: 0.43590
• Storage Temp.: Store at 0-5°C
• Solubility.: Chloroform, Methanol

Purity/Quality:

98%min ^*data from raw suppliers

N-tert-Butoxycarbonyl D-serine methyl ester ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Protected D-Serine.

Technology Process of BOC-D-SER-OME

There total 11 articles about BOC-D-SER-OME which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + R-(-)-serine methyl ester hydrochloride (5874-57-7) → 2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester (95715-85-8)

Guidance literature:

R-(-)-serine methyl ester hydrochloride; With triethylamine; In dichloromethane; for 0.5h; Cooling with ice;

di-tert-butyl dicarbonate; In dichloromethane; at 20 ℃; for 16.5h; Cooling with ice;

Reference yield: 100.0%

(R)-N-tert-butoxycarbonyl serine (3262-72-4,3850-40-6,6368-20-3,90582-28-8,84311-18-2) + methyl iodide (74-88-4) → 2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester (95715-85-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 25 ℃;

DOI:10.1021/ja00097a072

Reference yield: 98.0%

methanol (67-56-1) + D-Serine (312-84-5,83245-15-2) + di-tert-butyl dicarbonate (24424-99-5) → 2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester (95715-85-8)

Guidance literature:

methanol; D-Serine; With acetyl chloride; for 2h; Heating;

di-tert-butyl dicarbonate; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h; Further stages.;

DOI:10.1002/hlca.200790028

upstream raw materials:

diazomethane

(R)-N-tert-butoxycarbonyl serine

methyl iodide

di-tert-butyl dicarbonate

Downstream raw materials:

methyl (R)-3-azido-2-[(tert-butyloxycarbonyl)amino]propionate

(2R)-2-[N-(tert-butyloxycarbonyl)amino]-1-hydroxy-pentan-3-one

methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate

(S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester

Refernces

• 1、 Lynch, Dylan M.,McLean, Joshua T.,McSweeney, Lauren,Milbeo, Pierre,Scanlan, Eoin M.. "Radical-Mediated Acyl Thiol-Ene Reaction for Rapid Synthesis of Biomolecular Thioester Derivatives". supporting information. p. 4148 - 4160. Retrieved 2021/08/24.
• 2、 González-Gil, Inés,Zian, Debora,Vázquez-Villa, Henar,Hernández-Torres, Gloria,Martínez, R. Fernando,Khiar-Fernández, Nora,Rivera, Richard,Kihara, Yasuyuki,Devesa, Isabel,Mathivanan, Sakthikumar,Del Valle, Cristina Rosell,Zambrana-Infantes, Emma,Puigdomenech, María,Cincilla, Giovanni,Sanchez-Martinez, Melchor,Rodríguez De Fonseca, Fernando,Ferrer-Montiel, Antonio V.,Chun, Jerold,López-Vales, Rubén,López-Rodríguez, María L.,Ortega-Gutiérrez, Silvia. "A Novel Agonist of the Type 1 Lysophosphatidic Acid Receptor (LPA1), UCM-05194, Shows Efficacy in Neuropathic Pain Amelioration". supporting information. p. 2372 - 2390. Retrieved 2020/01/02.